Water → 5-Bromo-4-chloro-2,6-dimethoxypyrimidine

HRID 426272Notes

Reaction equation

HRID 426272 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[N:3]=1.C(=O)(O)[O-].[Na+].[Br:17]Br.O>CO>[Br:17][C:7]1[C:2]([Cl:1])=[N:3][C:4]([O:10][CH3:11])=[N:5][C:6]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 806004-Chloro-2,6-dimethoxypyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 122261955-Bromo-4-chloro-2,6-dimethoxypyrimidineYield 31.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-Chloro-2,6-dimethoxy-pyrimidine (2.2 g, 12.6 mmol) and sodium bicarbonate (2.39 g, 28.4 mmol) were stirred in aqueous methanol (50%, 40 mL) at room temperature. Bromine (3.52 g, 22.0 mmol) was added dropwise over a period of 60 minutes. After the addition was complete, stirring was continued or additional 60 minutes. The solid was collected and was washed with water to yield 6.2 g of crude material. 3.1 g of the crude material were dissolved in hot methanol (40 mL) and water (10 mL) was added. The resultant precipitate was collected and dried in vacuo to yield the product (1.0 g, 3.95 mmol). 1H (CDCl3): δ=4.05 (s, 3H), 3.99 (s, 3H) ppm.

Workup

  1. additionAfter the addition
  2. customThe solid was collected
  3. washwas washed with water
  4. customto yield 6.2 g of crude material
  5. customThe resultant precipitate was collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cebe0cd99c07439088102b7d398ac230
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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